Iron-Catalyzed Cross-Coupling Reactions between Arylzinc Reagents and Alkyl Halides Bearing β-Fluorines

We report the first example of iron-catalyzed cross-coupling of alpha-halo-beta,beta-difluoroethylene-containing compounds with arylzinc reagents using TMEDA and dppp as coligands. The reaction affords a wide range of functional group tolerant gem-difluoromethylenated compounds in moderate to good yields. The facile dehalodefluorination of alpha-halo-beta,beta-clifluoroethylenecontaining compounds upon treatment of reductive metal reagents was mostly inhibited. Mechanistic studies indicated that the cross-coupling reaction could involve a single-electron-transfer process.